Rayman is a complicated franchise. Well, technically it's a dead franchise... Or seems like one, anyway, given how much reverence Ubisoft seems to have for its best platforming series. But for a time Rayman was a complex web of multi-brand, multimedia nonsense you'd be hard-pressed to unravel.
It didn't start out that way, though. As one of the original PlayStation's early titles Rayman was a simple looking, hyperkinetic French fever dream of a game. One that looked like exactly the sort of thing you'd buy for your kid alongside a brand spanking new disc-based game console. What with its Saturday morning cartoon look and the fact that it played more-or-less like a game from the previous generation.
Of course, all of that was a camouflage for one of the toughest 2D platformers ever developed. Not for the reasons we're usually accustomed to, either.
The original Rayman is obtuse as hell. Your limbless hero begins the game with the ability to do two things: jack and shit. Rayman can't even attack until about two levels into the game, and bog-standard abilities in this sort of game -- like grabbing onto ledges, and running -- don't unlock until much further in than that. Then there's the fact that enemies spawn out of thin air, rather than appear onscreen in order to give you the time necessary to... Oh, what's the word? React.
Most of Rayman is spent blindly wandering into invisible enemy traps, getting your detached head kicked in, and trying again until you've memorized where to go and what to do. If that weren't enough the game is also full of passive obstacles, like spike traps and bottomless pits. Even all of that might be fine, were it not for the fact that lives and continues in Rayman are finite. If you don't make it to the final boss (which requires liberating every single one of the collectibles in the game just to unlock, mind you) in 25-odd lives or fewer you're shit out of luck.
So, Rayman was an absurdly difficult (not to mention just kind of bizarre) game that punishes pretty much everything you do. The next, logical step would of course be to turn that into a children's entertainment empire, no? No, but that's exactly what Ubisoft did. Rayman would eventually spawn the "Rabbids" (think Minions before Minions were a thing). These obnoxious branding vehicles made their way into no fewer than seven kids' games, as well as their own cartoon. Someone, somewhere is definitely upset Rayman didn't take off like those yellow usurping bastards did.
Counting Oregon Trail as a game is almost a bit of a cheat. "Games" typically have a set of internal logic and rules which can be followed in order to succeed. Games like Dark Souls make these rules incredibly strict, but fair (or so the argument goes). Oregon Trail is just a sequence of semi-random horrors, shit, and shit-based horrors aimed at kids with too much computer lab time.
If you're over a certain age, you've almost certainly played Oregon Trail (and remember what a "computer lab" is). So you know what we're talking about. Though they're probably still trying to brainwash modern kids with mobile versions of this old person's propaganda. It's tough to picture the previous generation giving up an opportunity to preach at youths about how much harder things were in the olden days at such a young age.
If, however, Oregon Trail has gone the way of every wagon tongue you never bought a spare for (that is, if it's gone) allow us to enlighten you.
This hot banger sent you and your fictional opportunity/land/gold/or something seeking family of 26 on a trek across early America. "Early" meaning white folks hadn't taken quite all of it yet, though that part suspiciously never came into play during the so-called educational game. Besides loading up on doomed offspring you also had to pick provisions and replacement parts for your covered wagon.
This was, of course, futile. Whatever you didn't bring in abundance was inevitably what ran out, broke down, or made a break for it and escaped into a better game first. If you've ever wondered where all the wall chickens in Castlevania came from, it's probably because they were tired of going rotten at the most inconvenient times in this game.
Ultimately, though, what would really kill you and yours was the random number generator. Literally. Quite often members of your family would just out-and-out die of horrible diseases or some such. The most famous and meme-able of which was dysentery. That's right, kids, the past wasn't just a complete waste of time -- it was rotten with a disease that would actually made you shit yourself to death. Very educational, indeed.